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(+)-Cerulenin

(+)-Cerulenin structure

CAS No:
17397-89-6
Formula:
C12H17NO3
Chemical Name:
(+)-Cerulenin
Synonyms:
2-Oxiranecarboxamide,3-[(4E,7E)-1-oxo-4,7-nonadien-1-yl]-,(2R,3S)-;7,10-Dodecadienamide,2,3-epoxy-4-oxo-;Oxiranecarboxamide,3-(1-oxo-4,7-nonadienyl)-,[2R-[2α,3α(4E,7E)]]-;Oxiranecarboxamide,3-[(4E,7E)-1-oxo-4,7-nonadienyl]-,(2R,3S)-;(2R,3S)-3-[(4E,7E)-1-Oxo-4,7-nonadien-1-yl]-2-oxiranecarboxamide;Cerulenin;Helicocerin;(+)-Cerulenin;11052-24-7;23557-85-9
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

White powderChEBI: An epoxydodecadienamide isolated from several species, including Acremonium, Acrocylindrum and Helicoceras. It inhibits the biosynthesis of several lipids by interfering with enzyme function.

Solid

(+)-Cerulenin Basic Attributes

Molecular Weight：

223.27

Exact Mass：

223.27

EC Number：

241-424-8

HScode：

29419090

Characteristics

PSA：

72.7

XLogP3：

1.2

Appearance：

White to off-white powder.

Density：

1.1223 (rough estimate)

Melting Point：

93.5 °C

Boiling Point：

bp 120° (10-8 mm)

Flash Point：

241.1±25.0 °C

Refractive Index：

1.5300 (estimate)

Water Solubility：

H2O: Slightly soluble ;acetone: 20 mg/mL, clear, colorless to yellow

Storage Conditions：

−20°C

Vapor Pressure：

1.66E-08mmHg at 25°C

Toxicity：

LD50 in mice (mg/kg): 154 i.v.; 211 i.p.; 547 orally (Matsumae 1964)

Specific rotation：

D16 +63° (c = 2 in methanol)

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

safety instructions：

24/25

RTECS Number：

JR1670000

Marks：

Precautionary statement(s)：

P264, P270, P301+P312, P330, P501

Hazard Statements：

H302

(+)-Cerulenin Use and Manufacturing

Cerulenin is an epoxy fatty acid amide isolated from the fungus Cephalosporium caerulens identified as an antifungal in the 1960s. Over the past 40 years, cerulenin has found broad application in lipid biochemistry as an inhibitor fatty acid and sterol biosynthesis. Cerulenin binds to β-keto-acyl-ACP synthase blocking the interaction of malonyl CoA. Cerulenin also an inhibits bacterial fatty acid synthesis, acting on the FabH, FabB and FabF condensation enzymes. Cerulenin stimulates fatty acid oxidation and inhibits HMG-CoA synthetase activity.

Computed Properties

Molecular Weight:223.27
XLogP3:0.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:7
Exact Mass:223.12084340
Monoisotopic Mass:223.12084340
Topological Polar Surface Area:72.7
Heavy Atom Count:16
Complexity:320
Defined Atom Stereocenter Count:2
Undefined Bond Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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Cerulenin 17397-89-6

CAS No.: 17397-89-6

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CERULENIN

CAS No.: 17397-89-6

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